A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities
Curcumin is a natural polyphenolic compound with well-known anticancer properties. Poor solubility and permeability hamper its use as an anticancer pharmaceutical product. In this study, L-arginine, a basic amino acid and a small hydrophilic molecule, was utilized to form a salt with the weak acid c...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/1/262 |
| _version_ | 1797406618490503168 |
|---|---|
| author | Adel Al Fatease Mai E. Shoman Mohammed A. S. Abourehab Heba A. Abou-Taleb Hamdy Abdelkader |
| author_facet | Adel Al Fatease Mai E. Shoman Mohammed A. S. Abourehab Heba A. Abou-Taleb Hamdy Abdelkader |
| author_sort | Adel Al Fatease |
| collection | DOAJ |
| description | Curcumin is a natural polyphenolic compound with well-known anticancer properties. Poor solubility and permeability hamper its use as an anticancer pharmaceutical product. In this study, L-arginine, a basic amino acid and a small hydrophilic molecule, was utilized to form a salt with the weak acid curcumin to enhance its solubility and potentiate the anticancer activities of curcumin. Two methods were adopted for the preparation of curcumin: L-arginine salt, namely, physical mixing and coprecipitation. The ion pair or salt was characterized for docking, solubility, DSC, FTIR, XRD, in vitro dissolution, and anticancer activities using MCF7 cell lines. The molecular docking suggested a salt/ion-pair complex between curcumin and L-arginine. Curcumin solubility was increased 335- and 440-fold by curcumin in L-arginine, physical, and co-precipitated mixtures, respectively. Thermal and spectral analyses supported the molecular docking and formation of a salt/ion pair between curcumin and L-arginine. The cytotoxicity of curcumin L-arginine salt significantly improved (<i>p</i> < 0.05) by 1.4-fold, as evidenced by the calculated IC<sub>50%</sub>, which was comparable to Taxol (the standard anticancer drug but with common side effects). |
| first_indexed | 2024-03-09T03:29:10Z |
| format | Article |
| id | doaj.art-1a4a4f7690ad478198e175fcd5003920 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T03:29:10Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1a4a4f7690ad478198e175fcd50039202023-12-03T14:57:24ZengMDPI AGMolecules1420-30492022-12-0128126210.3390/molecules28010262A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer ActivitiesAdel Al Fatease0Mai E. Shoman1Mohammed A. S. Abourehab2Heba A. Abou-Taleb3Hamdy Abdelkader4Department of Pharmaceutics, College of Pharmacy, King Khalid University, Abha 62529, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, Minia University, Minia 61519, EgyptDepartment of Pharmaceutics, College of Pharmacy, Umm Al-Qura University, Makkah 21955, Saudi ArabiaDepartment of Pharmaceutics and Industrial Pharmacy, Faculty of Pharmacy, Merit University (MUE), Sohag 82755, EgyptDepartment of Pharmaceutics, College of Pharmacy, King Khalid University, Abha 62529, Saudi ArabiaCurcumin is a natural polyphenolic compound with well-known anticancer properties. Poor solubility and permeability hamper its use as an anticancer pharmaceutical product. In this study, L-arginine, a basic amino acid and a small hydrophilic molecule, was utilized to form a salt with the weak acid curcumin to enhance its solubility and potentiate the anticancer activities of curcumin. Two methods were adopted for the preparation of curcumin: L-arginine salt, namely, physical mixing and coprecipitation. The ion pair or salt was characterized for docking, solubility, DSC, FTIR, XRD, in vitro dissolution, and anticancer activities using MCF7 cell lines. The molecular docking suggested a salt/ion-pair complex between curcumin and L-arginine. Curcumin solubility was increased 335- and 440-fold by curcumin in L-arginine, physical, and co-precipitated mixtures, respectively. Thermal and spectral analyses supported the molecular docking and formation of a salt/ion pair between curcumin and L-arginine. The cytotoxicity of curcumin L-arginine salt significantly improved (<i>p</i> < 0.05) by 1.4-fold, as evidenced by the calculated IC<sub>50%</sub>, which was comparable to Taxol (the standard anticancer drug but with common side effects).https://www.mdpi.com/1420-3049/28/1/262curcuminL-argininecytotoxicitybreast cancer |
| spellingShingle | Adel Al Fatease Mai E. Shoman Mohammed A. S. Abourehab Heba A. Abou-Taleb Hamdy Abdelkader A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities Molecules curcumin L-arginine cytotoxicity breast cancer |
| title | A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities |
| title_full | A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities |
| title_fullStr | A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities |
| title_full_unstemmed | A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities |
| title_short | A Novel Curcumin Arginine Salt: A Solution for Poor Solubility and Potential Anticancer Activities |
| title_sort | novel curcumin arginine salt a solution for poor solubility and potential anticancer activities |
| topic | curcumin L-arginine cytotoxicity breast cancer |
| url | https://www.mdpi.com/1420-3049/28/1/262 |
| work_keys_str_mv | AT adelalfatease anovelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT maieshoman anovelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT mohammedasabourehab anovelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT hebaaaboutaleb anovelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT hamdyabdelkader anovelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT adelalfatease novelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT maieshoman novelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT mohammedasabourehab novelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT hebaaaboutaleb novelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities AT hamdyabdelkader novelcurcuminargininesaltasolutionforpoorsolubilityandpotentialanticanceractivities |